Justin Higuchi from Los Angeles, CA, USA · CC BY 2.0

Lisa Loeb scored the first number-one Billboard Hot 100 single by an artist without a record deal with "Stay (I Missed You)" (1994), from the film Reality Bites, and followed it with gold albums Tails and Firecracker. She won a Grammy for Best Children's Music Album in 2016 for Feel What U Feel and now hosts a weekday show on SiriusXM.